# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2014

 
data_CD1013997 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             'Pd-alkyne cat' 
_chemical_melting_point           ? 
_chemical_formula_moiety          C20H35ClP2Pd 
_chemical_formula_sum 
 'C20 H35 Cl P2 Pd' 
_chemical_formula_weight          479.27 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'P'  'P'   0.1023   0.0942 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Pd'  'Pd'  -0.9988   1.0072 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    Pna2(1) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, z+1/2' 
 'x+1/2, -y+1/2, z' 
 '-x+1/2, y+1/2, z+1/2' 
 
_cell_length_a                    23.6604(11) 
_cell_length_b                    9.3856(4) 
_cell_length_c                    10.4813(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2327.55(18) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     3650 
_cell_measurement_theta_min       3.3820 
_cell_measurement_theta_max       28.0400 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.22 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.368 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              992 
_exptl_absorpt_coefficient_mu     1.050 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.86938 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
; 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'SuperNova (Mo) X-ray Source'' 
_diffrn_radiation_monochromator   'mirror' 
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at zero, Atlas' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  10.3914 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         none 
_diffrn_reflns_number             7787 
_diffrn_reflns_av_R_equivalents   0.0323 
_diffrn_reflns_av_sigmaI/netI     0.0465 
_diffrn_reflns_limit_h_min        -25 
_diffrn_reflns_limit_h_max        28 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.91 
_diffrn_reflns_theta_max          26.02 
_reflns_number_total              3646 
_reflns_number_gt                 3228 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;  
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
; 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
; 
_computing_publication_material   'SHELX-97 (Sheldrick, 1997)' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0178P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.00(3) 
_refine_ls_number_reflns          3646 
_refine_ls_number_parameters      223 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0374 
_refine_ls_R_factor_gt            0.0284 
_refine_ls_wR_factor_ref          0.0552 
_refine_ls_wR_factor_gt           0.0500 
_refine_ls_goodness_of_fit_ref    1.045 
_refine_ls_restrained_S_all       1.045 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.42652(16) 0.7598(3) 0.5578(5) 0.0269(10) Uani 1 1 d . . . 
C2 C 0.46803(17) 0.6868(4) 0.5412(4) 0.0290(12) Uani 1 1 d . . . 
C3 C 0.51961(18) 0.6092(3) 0.5201(4) 0.0286(11) Uani 1 1 d . . . 
C4 C 0.56382(17) 0.6153(4) 0.6061(4) 0.0331(13) Uani 1 1 d . . . 
H4 H 0.5598 0.6700 0.6818 0.040 Uiso 1 1 calc R . . 
C5 C 0.61391(17) 0.5431(4) 0.5834(7) 0.0434(11) Uani 1 1 d . . . 
H5 H 0.6439 0.5491 0.6433 0.052 Uiso 1 1 calc R . . 
C6 C 0.6203(2) 0.4630(5) 0.4753(6) 0.0474(13) Uani 1 1 d . . . 
H6 H 0.6545 0.4122 0.4609 0.057 Uiso 1 1 calc R . . 
C7 C 0.5774(2) 0.4564(5) 0.3880(5) 0.0423(12) Uani 1 1 d . . . 
H7 H 0.5823 0.4028 0.3119 0.051 Uiso 1 1 calc R . . 
C8 C 0.5273(2) 0.5267(4) 0.4096(5) 0.0356(11) Uani 1 1 d . . . 
H8 H 0.4976 0.5195 0.3490 0.043 Uiso 1 1 calc R . . 
C9 C 0.41201(17) 1.2299(3) 0.5873(6) 0.0352(11) Uani 1 1 d . . . 
H9A H 0.3721 1.2617 0.5903 0.042 Uiso 1 1 calc R . . 
H9B H 0.4351 1.3012 0.6334 0.042 Uiso 1 1 calc R . . 
C10 C 0.4311(2) 1.2231(5) 0.4500(5) 0.0496(14) Uani 1 1 d . . . 
H10A H 0.4709 1.1943 0.4466 0.074 Uiso 1 1 calc R . . 
H10B H 0.4268 1.3172 0.4105 0.074 Uiso 1 1 calc R . . 
H10C H 0.4081 1.1536 0.4036 0.074 Uiso 1 1 calc R . . 
C11 C 0.49329(17) 1.0200(4) 0.6754(5) 0.0372(11) Uani 1 1 d . . . 
H11A H 0.4989 0.9373 0.7326 0.045 Uiso 1 1 calc R . . 
H11B H 0.5060 0.9912 0.5892 0.045 Uiso 1 1 calc R . . 
C12 C 0.5314(2) 1.1413(5) 0.7215(6) 0.0604(16) Uani 1 1 d . . . 
H12A H 0.5272 1.2234 0.6645 0.091 Uiso 1 1 calc R . . 
H12B H 0.5708 1.1095 0.7212 0.091 Uiso 1 1 calc R . . 
H12C H 0.5205 1.1686 0.8083 0.091 Uiso 1 1 calc R . . 
C13 C 0.3966(2) 1.0972(4) 0.8307(5) 0.0364(11) Uani 1 1 d . . . 
H13A H 0.4252 1.1599 0.8705 0.044 Uiso 1 1 calc R . . 
H13B H 0.3604 1.1501 0.8286 0.044 Uiso 1 1 calc R . . 
C14 C 0.3893(2) 0.9656(5) 0.9129(5) 0.0536(14) Uani 1 1 d . . . 
H14A H 0.3594 0.9053 0.8769 0.080 Uiso 1 1 calc R . . 
H14B H 0.3788 0.9942 0.9997 0.080 Uiso 1 1 calc R . . 
H14C H 0.4248 0.9122 0.9154 0.080 Uiso 1 1 calc R . . 
C15 C 0.26606(17) 0.7675(4) 0.3486(4) 0.0286(10) Uani 1 1 d . . . 
H15A H 0.2415 0.6884 0.3196 0.034 Uiso 1 1 calc R . . 
H15B H 0.2414 0.8497 0.3691 0.034 Uiso 1 1 calc R . . 
C16 C 0.30601(19) 0.8090(4) 0.2404(5) 0.0378(11) Uani 1 1 d . . . 
H16A H 0.3281 0.8927 0.2658 0.057 Uiso 1 1 calc R . . 
H16B H 0.2840 0.8316 0.1639 0.057 Uiso 1 1 calc R . . 
H16C H 0.3316 0.7295 0.2221 0.057 Uiso 1 1 calc R . . 
C17 C 0.24756(18) 0.6740(4) 0.6056(4) 0.0356(14) Uani 1 1 d . . . 
H17A H 0.2232 0.7591 0.6154 0.043 Uiso 1 1 calc R . . 
H17B H 0.2238 0.5955 0.5723 0.043 Uiso 1 1 calc R . . 
C18 C 0.2709(2) 0.6318(4) 0.7358(5) 0.0450(13) Uani 1 1 d . . . 
H18A H 0.2950 0.5475 0.7266 0.068 Uiso 1 1 calc R . . 
H18B H 0.2395 0.6100 0.7936 0.068 Uiso 1 1 calc R . . 
H18C H 0.2931 0.7106 0.7708 0.068 Uiso 1 1 calc R . . 
C19 C 0.33500(18) 0.5414(4) 0.4516(5) 0.0327(11) Uani 1 1 d . . . 
H19A H 0.3640 0.5574 0.3851 0.039 Uiso 1 1 calc R . . 
H19B H 0.3546 0.5049 0.5283 0.039 Uiso 1 1 calc R . . 
C20 C 0.2947(2) 0.4267(4) 0.4044(5) 0.0401(12) Uani 1 1 d . . . 
H20A H 0.2660 0.4080 0.4698 0.060 Uiso 1 1 calc R . . 
H20B H 0.3158 0.3391 0.3869 0.060 Uiso 1 1 calc R . . 
H20C H 0.2761 0.4592 0.3260 0.060 Uiso 1 1 calc R . . 
Cl1 Cl 0.28380(4) 1.04122(9) 0.58562(16) 0.0326(2) Uani 1 1 d . . . 
P1 P 0.41812(4) 1.05820(10) 0.66800(11) 0.0258(2) Uani 1 1 d . . . 
P2 P 0.30315(4) 0.71300(10) 0.49145(12) 0.0246(2) Uani 1 1 d . . . 
Pd1 Pd 0.361697(10) 0.88619(2) 0.57433(5) 0.02164(8) Uani 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.210(5) . ? 
C1 Pd1 1.947(4) . ? 
C2 C3 1.439(5) . ? 
C3 C4 1.382(6) . ? 
C3 C8 1.405(6) . ? 
C4 C5 1.386(5) . ? 
C5 C6 1.368(8) . ? 
C6 C7 1.367(7) . ? 
C7 C8 1.375(6) . ? 
C9 C10 1.511(8) . ? 
C9 P1 1.825(4) . ? 
C11 C12 1.530(6) . ? 
C11 P1 1.816(4) . ? 
C13 C14 1.516(6) . ? 
C13 P1 1.817(5) . ? 
C15 C16 1.527(6) . ? 
C15 P2 1.809(4) . ? 
C17 C18 1.524(7) . ? 
C17 P2 1.815(4) . ? 
C19 C20 1.522(5) . ? 
C19 P2 1.826(4) . ? 
Cl1 Pd1 2.3512(8) . ? 
P1 Pd1 2.3136(10) . ? 
P2 Pd1 2.3055(10) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 Pd1 175.8(4) . . ? 
C1 C2 C3 176.0(4) . . ? 
C4 C3 C8 117.5(4) . . ? 
C4 C3 C2 121.4(4) . . ? 
C8 C3 C2 121.1(4) . . ? 
C3 C4 C5 121.0(5) . . ? 
C6 C5 C4 120.4(5) . . ? 
C5 C6 C7 119.8(4) . . ? 
C6 C7 C8 120.5(4) . . ? 
C7 C8 C3 120.8(4) . . ? 
C10 C9 P1 112.4(3) . . ? 
C12 C11 P1 116.3(3) . . ? 
C14 C13 P1 113.7(3) . . ? 
C16 C15 P2 112.7(3) . . ? 
C18 C17 P2 112.4(3) . . ? 
C20 C19 P2 116.1(3) . . ? 
C11 P1 C13 105.9(2) . . ? 
C11 P1 C9 105.8(2) . . ? 
C13 P1 C9 103.6(2) . . ? 
C11 P1 Pd1 116.46(14) . . ? 
C13 P1 Pd1 112.14(15) . . ? 
C9 P1 Pd1 111.94(17) . . ? 
C15 P2 C17 104.5(2) . . ? 
C15 P2 C19 105.1(2) . . ? 
C17 P2 C19 105.77(19) . . ? 
C15 P2 Pd1 113.82(13) . . ? 
C17 P2 Pd1 109.21(14) . . ? 
C19 P2 Pd1 117.38(14) . . ? 
C1 Pd1 P2 90.58(12) . . ? 
C1 Pd1 P1 90.48(12) . . ? 
P2 Pd1 P1 176.92(5) . . ? 
C1 Pd1 Cl1 177.71(17) . . ? 
P2 Pd1 Cl1 89.10(4) . . ? 
P1 Pd1 Cl1 89.95(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              26.02 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.328 
_refine_diff_density_min   -0.402 
_refine_diff_density_rms    0.070 
